2,3,4,5-Tetrahydro-1-benzoxepin-5-ol → 2,3-Dihydrobenzo[b]oxepine

HRID 1613607ノート

反応式

HRID 1613607 の反応式
O[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:2]=[CH:3][CH2:4][CH2:5]1

参加物

4

反応物 2

HCID 3155762,3,4,5-Tetrahydro-1-benzoxepin-5-olHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 2567432,3-Dihydrobenzo[b]oxepine収率 93.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

800 ml of toluene are poured over 53 g (0.323 mole) of 5-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin and, with addition of 3.7 g of p-toluenesulfonic acid monohydrate, the mixture is refluxed with a water trap for 1.5 hours. The cold organic phase is washed with saturated sodium bicarbonate solution, water and sodium chloride solution, and the solvent is evaporated off in vacuo. Kugelrohr distillation at 30°-35° C./0.008 torr results in 44 g of oil. p 1H NMR (60 MHz/CDCl3): δ=7.23-6.70 (m, 4H); δ=6.30 (m, 1H); δ=6.07-5.70 (m, 1H); δ=4.20 (t, J=5 Hz, 2H); δ=2.63 (m, 2H).

後処理

  1. temperaturethe mixture is refluxed with a water trap for 1.5 hours
  2. washThe cold organic phase is washed with saturated sodium bicarbonate solution, water and sodium chloride solution
  3. customthe solvent is evaporated off in vacuo
  4. distillationKugelrohr distillation at 30°-35° C./0.008 torr

出典と根拠

ORDレコード
ord-ce587cc7bc8b47cfb12635ddaa4c4cfe
出典データセット
uspto-grants-1993_03
特許番号
US05194442

反応ノート

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